1-Hexene → HCID 69538214, compound

HRID 2216272Notes

Reaction equation

HRID 2216272 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH2:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH3:34]>>[CH:29](/[C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[N:6]=[C:7]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])=[CH:30]\[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

3

Reactant 2

HCID 115971-HexeneHCID 86592816HCID 86592816, compound

Product 1

HCID 69538214HCID 69538214, compound

Procedure

The reaction was performed with 2-iodo-8-benzylaminoadenosine (11, 410 mg, 0.82 mmol) and (E)-1-borocatechol)-1-hexene (2.47 mmol). The mixture was purified by column chromatography (10% MeOH in CH2Cl2). Yield 41 mg (0.10 mmol, 11%), mp 153–155÷C; 1H NMR (MeOD-d4) δ 7.64 (t, 1H, J=6.10 Hz, NH), 7.36–7.18 (m, 5H, phenyl), 6.59 (bs, 2H, NH2), 6.94–6.80 (m, 1H, ═CHCH2), 6.28 (d, 1H, J=15.42 Hz, ═CH), 5.92 (d, 1H, J=7.71 Hz, H-1′), 5.77 (t, 1H, J=4.85 Hz, OH-2′), 5.32 (d, 1H, J=6.74 Hz, OH-5′), 5.18 (d, 1H, J=4.18 Hz, OH-3′), 4.64 (q, 1H, J=4.64 Hz, H-2′), 4.58 (t, 2H, J=4.65 Hz, NHCH2), 4.09 (t, 1H, J=4.09 Hz, H-3′), 3.98 (d, 1H, J=1.60 Hz, H-4′), 3.62 (q, 2H, J=2.58 Hz, H-5′), 2.29–2.05 (m, 2H, ═CHCH2), 1.72–1.20 (m, 4H, CH2CH2), 1.00–0.83 (m, 3H, CH3) ppm; MS m/z 456 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=9.61 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=26.10 min.

Workup

  1. customThe mixture was purified by column chromatography (10% MeOH in CH2Cl2)
  2. waitSystem B: 30–100% CH3OH in H2O in 40 min.

Sources & evidence

ORD record
ord-a39cfb0a099140969f35a9faf7472f4e
Source dataset
uspto-grants-2006_09
Patent number
US07112574B2

Reaction notes

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